Home Quinolines 16562-13-3
16562-13-3,MFCD00211195
Catalog No.:AA001W6O

16562-13-3 | 6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (13aS)-

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1mg
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5mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001W6O
Chemical Name:
6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (13aS)-
CAS Number:
16562-13-3
Molecular Formula:
C19H21NO4
Molecular Weight:
327.3743
MDL Number:
MFCD00211195
SMILES:
COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(OC)c(cc1)O
Properties
Computed Properties
 
Complexity:
447  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
2.6  

Literature

Title: (-)-Stepholidine is a potent pan-dopamine receptor antagonist of both G protein- and β-arrestin-mediated signaling.

Journal: Psychopharmacology 20150301

Title: Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: selective inhibitors of dopamine D₁ receptor.

Journal: Bioorganic & medicinal chemistry 20120801

Title: l-Stepholidine-induced excitation of dopamine neurons in rat ventral tegmental area is associated with its 5-HT(1A) receptor partial agonistic activity.

Journal: Synapse (New York, N.Y.) 20110501

Title: L-stepholidine reduced L-DOPA-induced dyskinesia in 6-OHDA-lesioned rat model of Parkinson's disease.

Journal: Neurobiology of aging 20100601

Title: Enantioselective total synthesis of (-)-(S)-stepholidine.

Journal: The Journal of organic chemistry 20091204

Title: D(1)/D(2) receptor-targeting L-stepholidine, an active ingredient of the Chinese herb Stephonia, induces non-rapid eye movement sleep in mice.

Journal: Pharmacology, biochemistry, and behavior 20091101

Title: Evaluation of the antipsychotic effect of bi-acetylated l-stepholidine (l-SPD-A), a novel dopamine and serotonin receptor dual ligand.

Journal: Schizophrenia research 20091101

Title: Oral bioavailability and brain penetration of (-)-stepholidine, a tetrahydroprotoberberine agonist at dopamine D(1) and antagonist at D(2) receptors, in rats.

Journal: British journal of pharmacology 20091101

Title: Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?

Journal: Bioorganic & medicinal chemistry 20091001

Title: [Five alkaloids from vine stems of Diploclisia affinis].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081101

Title: The antipsychotic potential of l-stepholidine--a naturally occurring dopamine receptor D1 agonist and D2 antagonist.

Journal: Psychopharmacology 20080801

Title: Recent development in studies of tetrahydroprotoberberines: mechanism in antinociception and drug addiction.

Journal: Cellular and molecular neurobiology 20080601

Title: Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: molecular modeling and dynamics simulations.

Journal: Biophysical journal 20070901

Title: Effects of (-)-stepholidine on NMDA receptors: comparison with haloperidol and clozapine.

Journal: Acta pharmacologica Sinica 20070701

Title: Quantification of l-stepholidine in rat brain and plasma by high performance liquid chromatography combined with fluorescence detection.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070501

Title: l-Stepholidine increases the frequency of sEPSC via the activation of D1 dopamine signaling pathway in rat prelimbic cortical neurons.

Journal: Acta pharmacologica Sinica 20070501

Title: The effect of L-stepholidine, a novel extract of Chinese herb, on the acquisition, expression, maintenance, and re-acquisition of morphine conditioned place preference in rats.

Journal: Neuropharmacology 20070201

Title: Recent developments in studies of l-stepholidine and its analogs: chemistry, pharmacology and clinical implications.

Journal: Current medicinal chemistry 20070101

Title: Effects of (-)stepholidine in animal models for schizophrenia.

Journal: Acta pharmacologica Sinica 20060901

Title: Stepholidine protects against H2O2 neurotoxicity in rat cortical neurons by activation of Akt.

Journal: Neuroscience letters 20050805

Title: Effects of l-stepholidine on forebrain Fos expression: comparison with clozapine and haloperidol.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050201

Title: Recent pharmacological studies on natural products in China.

Journal: European journal of pharmacology 20041001

Title: (-)-Stepholidine promotes proliferation and neuronal differentiation of rat embryonic striatal precursor cells in vitro.

Journal: Neuroreport 20021115

Title: (-)-Stepholidine: a potential novel antipsychotic drug with dual D1 receptor agonist and D2 receptor antagonist actions.

Journal: Trends in pharmacological sciences 20020101

Title: Ma B, et al. L-stepholidine, a natural dopamine receptor D1 agonist and D2 antagonist, inhibits heroin-induced reinstatement. Neurosci Lett. 2014 Jan 24;559:67-71.

Title: Zhou M, et al. The Neuroprotective Effect of L-Stepholidine on Methamphetamine-Induced Memory Deficits in Mice. Neurotox Res. 2019 Aug;36(2):376-386.

Title: Wang W, et al. The effect of L-stepholidine, a novel extract of Chinese herb, on the acquisition, expression, maintenance, and re-acquisition of morphine conditioned place preference in rats. Neuropharmacology. 2007 Feb;52(2):355-61. Epub 2006 Oct 5.

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Tags:16562-13-3 Molecular Formula|16562-13-3 MDL|16562-13-3 SMILES|16562-13-3 6H-Dibenzo[a,g]quinolizine-2,10-diol, 5,8,13,13a-tetrahydro-3,9-dimethoxy-, (13aS)-